Kuwanon V

Details

• Internal ID: 624b1f39-ae45-43a1-a516-e7571354efea
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (E)-1-[3-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• InChI: InChI=1S/C40H38O8/c1-22(2)4-14-29-35(45)20-26(21-36(29)46)39(47)37-31(25-8-12-28(42)13-9-25)18-23(3)19-32(37)38-34(44)17-15-30(40(38)48)33(43)16-7-24-5-10-27(41)11-6-24/h4-13,15-17,19-21,31-32,37,41-42,44-46,48H,14,18H2,1-3H3/b16-7+/t31-,32+,37-/m1/s1
• InChI Key: MYKDNKGHXHALEF-SJIVMEQQSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₃₈O₈
• Molecular Weight: 646.70 g/mol
• Exact Mass: 646.25666817 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 8.00
• Atomic LogP (AlogP): 8.04
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• (E)-1-(3-((1S,5S,6R)-6-(3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl)-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl)-2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-1-[3-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• (e)-2',4,4'-Trihydroxy-3'-(3-methyl-5a-(4-hydroxyphenyl)-6b-(2,4-dihydroxy-3-(3-methyl-2-butenyl)benzoyl)-2-cyclohexene-1b-yl)chalcone
• (e)-2',4,4'-Trihydroxy-3'-(3-methyl-5I+--(4-hydroxyphenyl)-6I2-(2,4-dihydroxy-3-(3-methyl-2-butenyl)benzoyl)-2-cyclohexene-1I2-yl)chalcone
• (e)-2',4,4'-Trihydroxy-3'-[3-methyl-5a-(4-hydroxyphenyl)-6b-[2,4-dihydroxy-3-(3-methyl-2-butenyl)benzoyl]-2-cyclohexene-1b-yl]chalcone
• (e)-2',4,4'-Trihydroxy-3'-[3-methyl-5I+--(4-hydroxyphenyl)-6I2-[2,4-dihydroxy-3-(3-methyl-2-butenyl)benzoyl]-2-cyclohexene-1I2-yl]chalcone
• RefChem:151575
• CHEMBL570609
• BDBM50303003

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.8709	87.09%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7948	79.48%
OATP2B1 inhibitior	+	0.5746	57.46%
OATP1B1 inhibitior	+	0.8090	80.90%
OATP1B3 inhibitior	+	0.8368	83.68%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9434	94.34%
P-glycoprotein inhibitior	+	0.7964	79.64%
P-glycoprotein substrate	+	0.5855	58.55%
CYP3A4 substrate	+	0.6306	63.06%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.6784	67.84%
CYP2C9 inhibition	+	0.8534	85.34%
CYP2C19 inhibition	+	0.8216	82.16%
CYP2D6 inhibition	-	0.7485	74.85%
CYP1A2 inhibition	+	0.8759	87.59%
CYP2C8 inhibition	+	0.8449	84.49%
CYP inhibitory promiscuity	+	0.8124	81.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7483	74.83%
Carcinogenicity (trinary)	Non-required	0.7151	71.51%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.8062	80.62%
Skin corrosion	-	0.9000	90.00%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8910	89.10%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.5484	54.84%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8359	83.59%
Acute Oral Toxicity (c)	III	0.6065	60.65%
Estrogen receptor binding	+	0.8251	82.51%
Androgen receptor binding	+	0.8476	84.76%
Thyroid receptor binding	+	0.6136	61.36%
Glucocorticoid receptor binding	+	0.7736	77.36%
Aromatase binding	-	0.5489	54.89%
PPAR gamma	+	0.7723	77.23%
Honey bee toxicity	-	0.7923	79.23%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	13800 nM	IC50	PMID: 19846295

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.17%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.84%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.89%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.52%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.84%	86.33%
CHEMBL3194	P02766	Transthyretin	90.80%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.45%	90.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.19%	85.00%
CHEMBL4208	P20618	Proteasome component C5	87.74%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.33%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.31%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.29%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.74%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.68%	91.71%
CHEMBL206	P03372	Estrogen receptor alpha	85.74%	97.64%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.53%	97.21%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.74%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.25%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.21%	96.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.03%	93.99%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.08%	95.17%
CHEMBL2535	P11166	Glucose transporter	81.04%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.17%	92.94%

Plants that contains it

• Morus alba

Cross-Links

• PubChem: 45485203
• NPASS: NPC85393
• ChEMBL: CHEMBL570609
• LOTUS: LTS0164297
• wikiData: Q105174969